Dimethylformamide → Methyl 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinate

https://huagongshe.com/reaction/2080273

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Cyanophenylboronic acid	HCID 2734610	—
Reactant	Chloride methyl 6-chloro-2-(3-fluorophenethylamino)nicotinate	HCID 86626130	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	Methyl 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinate	HCID 57542380	82%
Product	6-(2-cyanophenyl)-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide	HCID 57542525	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of chloride methyl 6-chloro-2-(3-fluorophenethylamino)nicotinate (30.8 g, 0.1 mol), 2-cyanophenyl boronic acid (17.6 g, 0.12 mol), PdCl2(dppf)2 (3.6 g, 5.0 mmol), K2CO3 (41.4 g, 0.3 mol) and anhydrous DMF (100 mL) was degassed with nitrogen for 30 min. The mixture was then stirred at 100° C. for 2 hrs. The mixture was filtered through the Celite and washed with EtOAc. The filtrate was diluted with EtOAc, washed with brine and concentrated to dryness. The residue was purified by silica gel flash chromatography using hexane-EtOAc (4:1) as eluant to give the desired product methyl 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinate as a yellow solid (31 g, 82%). LRMS (M+H+) m/z 376.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07932270B2
Source dataset	uspto-grants-2011_04
ORD ID	ord-f5e187d44544445d97e35997c9398d3e
Source note	uspto-grants-2011_04